Aluminium lithium hydride → 3-{4-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazin-1-ylmethyl}-morpholine-4-carboxylic acid tert-butyl ester

HRID 2047378Notes

Reaction equation

HRID 2047378 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[N:32]([CH3:33])[C:31]4[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=4[N:29]=3)[CH:23]=2)[CH2:18][CH2:17]1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[CH2:14][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[N:32]([CH3:33])[C:31]4[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=4[N:29]=3)[CH:23]=2)[CH2:18][CH2:17]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 686711193-{4-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazine-1-carbonyl}-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 686701863-{4-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazin-1-ylmethyl}-morpholine-4-carboxylic acid tert-butyl esterYield 43.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{4-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazine-1-carbonyl}-morpholine-4-carboxylic acid tert-butyl ester (0.21 g, 0.42 mmol) in dry THF (3 mL) at room temperature under a nitrogen atmosphere was added lithium aluminium hydride (LiAlH4) (0.05 g, 1.27 mmol). The reaction was heated at reflux for 2 h. The solution was then cooled to room temperature, quenched with 15% NaOH and then extracted with dichloromethane (3×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude was then purified by Preparative HPLC to obtain 0.09 g (43%) of the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 h
  3. customquenched with 15% NaOH
  4. extractionextracted with dichloromethane (3×10 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude was then purified by Preparative HPLC

Sources & evidence

ORD record
ord-859e2c8882bd476188cbd34e3924e1a4
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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